I have a Debian 9 box, and if I plug in 1 of my devices, its UART shows up in both lsusb and in the output of ls /sys/bus/usb-serial/devices/.
When I attach 2, the 2nd one always shows up.
But for some number greater than 2, no new entries appear in lsusb or usb-serial/devices/. It also seems to be kind of random: sometimes the 3rd device will show up, sometimes not.
This behavior is the same across 3 different brands of USB hub. I also tried connecting these devices on MacOS, and got a similar behavior.
Currently my lsusb looks like this (other hubs and devices omitted for clarity):
... snip
Bus 001 Device 042: ID 0403:6014 Future Technology Devices International, Ltd FT232H Single HS USB-UART/FIFO IC
Bus 001 Device 040: ID 0403:6014 Future Technology Devices International, Ltd FT232H Single HS USB-UART/FIFO IC
Bus 001 Device 036: ID 05e3:0610 Genesys Logic, Inc. 4-port hub
Bus 001 Device 039: ID 10c4:ea71 Cygnal Integrated Products, Inc.
Bus 001 Device 037: ID 0403:6014 Future Technology Devices International, Ltd FT232H Single HS USB-UART/FIFO IC
... snip
Is there some system setting preventing the additional devices from showing up?